Process for the preparation of new derivatives of naphthoquinone



Patented Jan. 31, 192.

UNITED STATES ANDRE WAHL, OF ENGHIEN,

ONE-HALF TO SOCIETE ANONYME DES MATIERES CHIMIQUES DE SAINT-DENIS, F PARIS, FRANCE.

PROCESS FOR THE PREPARATION OF DERIVATIVES OF NAPHTHOQUINONE.

No Drawing. Original application filed December 21, 1922, Serial No. 608,334,

and in 28, 1921. Divided and this application filed July 12, 1924. Serial No. 725,669.

own g +Nmso.=omH These new sulphonic acids form crystals which are slightly coloured gray, little soluble in water, soluble in the alkaline bodies with which they form salts.

The following examples will serve to show these differenttransformations, but it is ob vious that the conditions under which they can take place can be largely modified.

Example 1. Sulphomlc acid 0 an hydrowy arylamino naphthalene. mixture of 40 grs. of 1-phenylimino-Q-naphthoquinone, freshly prepared and pressed, and 55 cc. of a solution of bisulphite of sodium of 36 B., are triturated in a mortar, at the ordinary temperature. The green col0ration of the phenylimino-naphthoquinone disappears by and by and there is formed a gray crystalline precipitate. \Vhenthe re-- action is complete, the operation is repeated with a concentrated solution of carbonate of sodium, filtered and acidified by a mineral acid. The product of the reaction is precipitated in the form of small gray crystals which can be re-crystallized in dilute alcohol containing hydrochloric acid.

The reaction is as follows:

NCH no (10H0 0 lN.HS0l=C1oH S (1):E am

AND ROBERT LANTZ, 0F IPA'RIS, FRANCE, ASSIGNOBS OF COLORANTES E1 PRODUITS Germany December for the free acid, the analysis gives the following figures Calculated for Found uHn nN The free acid forms colourless crystals, little soluble in water; its sodium salt is very soluble and its solutions have a very great green fluorescence.

By substituting for the l-phenylimino 2- naphthoquinone, its homologous or its direct derivatives, a similar reaction can be obtained.

What we claim is:

1. A process of preparing sulphonic acids of 1-ary1imino-2-hydroxy-naphthalene which consists in treating the 1-arylimino-2-naph thoguinones with soluble salts of sulphurous ac1 2. A process of preparing sulphonic acids of 1-arylimino-2-hydroxy-naphthalene which consists in treating the 1-arylimino-2-naphthoquinones with neutral soluble salts of sulphurous acid.

8. As new products, the sul honic acids of 1-arylimino-2-hydroxy-napht alene.

In testimony whereof we have signed this specification.

ANDRE WAHL. ROBERT LANTZ. 

